Photoinitiated by red light (625 nm) iodosulfonylation of internal alkynes to synthesize β-iodovinylsulfones

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Resumo

Synthesis of β-iodovinyl sulfones was performed out by direct bifunctionalization of internal alkynes using an economical LED light source with a maximum emission wavelength of 625 nm. The products were obtained in high yields (68 to 99%) using equivalent amounts of reagents. The reaction of arylsulfonyl iodides with internal alkynes proceeds by a radical mechanism and is a regioselective method for the synthesis of β-iodovinyl sulfones.

Sobre autores

V. Abramov

Topchiev Institiute of Petrochemical Synthesis, Russian Academy of Sciences

M. Topchiy

Topchiev Institiute of Petrochemical Synthesis, Russian Academy of Sciences

A. Malysheva

Topchiev Institiute of Petrochemical Synthesis, Russian Academy of Sciences

I. Beletskaya

Topchiev Institiute of Petrochemical Synthesis, Russian Academy of Sciences

A. Asachenko

Topchiev Institiute of Petrochemical Synthesis, Russian Academy of Sciences

Email: aasachenko@ips.ac.ru

Bibliografia

  1. Beletskaya I.P., Ananikov V.P. Chem. Rev. 2011, 111, 1596-1636. doi: 10.1021/cr100347k
  2. Beletskaya I.P., Ananikov V.P. Chem. Rev. 2022, 122, 16110-16293. doi: 10.1021/acs.chemrev.1c00836
  3. Tatevosyan S.S., Kotovshchikov Y.N., Latyshev G.V., Erzunov D.A., Sokolova D.V., Beletskaya I.P., Lukashev N.V. J. Org. Chem. 2020, 85, 7863-7876. doi: 10.1021/acs.joc.0c00520
  4. Gevondian A.G., Kotovshchikov Y.N., Latyshev G.V, Lukashev N.V., Beletskaya I.P. J. Org. Chem. 2021, 86, 5639-5650. doi: 10.1021/acs.joc.1c00115
  5. Burykina J.V., Kobelev A.D., Shlapakov N.S., Kostyukovich A.Y., Fakhrutdinov A.N., K�nig B., Ananikov V.P. Angew. Chem., Int. Ed. 2022, 61, e202116888. doi: 10.1002/anie.202116888
  6. Scott K.A., Njardarson J.T. Top. Curr. Chem. 2018, 376, 5. doi: 10.1007/s41061-018-0184-5
  7. Reddy R.J., Kumari A.H. RSC Adv. 2021, 11, 9130-9221. doi: 10.1039/D0RA09759D
  8. Padma Priya V.R., Natarajan K., Nandi G.C. Tetrahedron. 2022, 111, 132711. doi: 10.1016/j.tet.2022.132711
  9. Dong B., Shen J., Xie L.-G. Org. Chem. Front. 2023, 10, 1322-1345. doi: 10.1039/D2QO01699K
  10. Reddy R.J., Kumar J.J., Kumari A.H., Krishna G.R. Adv. Synth. Catal. 2020, 362, 1317-1322. doi: 10.1002/adsc.201901550
  11. Reddy R.J., Kumar J.J., Kumari A.H. Eur. J. Org. Chem. 2019, 2019, 3771-3775. doi: 10.1002/ejoc.201900676
  12. Reddy R.J., Kumari A.H., Sharadha N., Krishna G.R. J. Org. Chem. 2022, 87, 3934-3951. doi: 10.1021/acs.joc.1c02444
  13. Reddy R.J., Sharadha N., Krishna G.R. J. Org. Chem. 2023, 88, 8889-8903. doi: 10.1021/acs.joc.3c00671
  14. Fang Y., Luo Z., Xu X. RSC Adv. 2016, 6, 59661-59676. doi: 10.1039/C6RA10731A
  15. Li X.-Q., Liao Q.-Q., Lai J., Liao Y.-Y. Front. Chem. 2023, 11, 1267223. doi: 10.3389/fchem.2023.1267223
  16. Mulina O.M., Ilovaisky A.I., Parshin V.D., Terent'ev A.O. Adv. Synth. Catal. 2020, 362, 4579-4654. doi: 10.1002/adsc.202000708
  17. Kumar S., Kumar J., Naqvi T., Raheem S., Rizvi M.A., Shah B.A. ChemPhotoChem. 2022, 6, e202200110. doi: 10.1002/cptc.202200110
  18. Kumar R., Dwivedi V., Sridhar Reddy M. Adv. Synth. Catal. 2017, 359, 2847-2856. doi: 10.1002/adsc.201700576
  19. Gurawa A., Kumar N., Kashyap S. Org. Chem. Front. 2023, 10, 4918-4926. doi: 10.1039/D3QO01188G
  20. Tong C., Gan B., Yan Y., Xie Y.-Y. Synth. Commun. 2017, 47, 1927-1933. doi: 10.1080/00397911.2017.1337152
  21. Truce W.E., Wolf G.C. J. Org. Chem. 1971, 36, 1727-1732. doi: 10.1021/jo00812a001
  22. Abramov V.A., Topchiy M.A., Rasskazova M.A., Drokin E.A., Sterligov G.K., Shurupova O.V., Malysheva A.S., Rzhevskiy S.A., Beletskaya I.P., Asachenko A.F. Org. Biomol. Chem. 2023, 21, 3844-3849. doi: 10.1039/D3OB00437F
  23. Cao L., Luo S.-H., Jiang K., Hao Z.-F., Wang B.-W, Pang C.-M., Wang Z.-Y. Org. Lett. 2018, 20, 4754-4758. doi: 10.1021/acs.orglett.8b01808
  24. Peng C., Gu F., Lin X., Ding N., Zhan Q., Cao P., Cao T. Green Chem. 2023, 25, 671-677. doi: 10.1039/D2GC04296G
  25. Ma Y., Wang K., Zhang D., Sun P. Adv. Synth. Catal. 2019, 361, 597-602. doi: 10.1002/adsc.201801258

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